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Photocatalytic C-C Coupling by a Au(I) Complex: Mechanistic Elucidation and SET Modulation.

Yan Jiang1, Le-Jie Liu1, Jia-Jia Ma2

  • 1Shaanxi Provincial Key Laboratory of New Concept Sensors and Molecular Materials, Key Laboratory of Applied Surface and Colloids Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

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This study reveals how gold catalysts drive photocatalytic C-C coupling reactions through a triplet-state mechanism involving electron transfer. Modifying catalysts with electron-withdrawing groups enhances efficiency and offers a framework for developing cost-effective silver and copper alternatives.

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Area of Science:

  • Organometallic Chemistry
  • Photocatalysis
  • Computational Chemistry

Background:

  • Photocatalytic C-C coupling reactions are crucial in synthetic chemistry.
  • Gold (Au)-based catalysts show promise in these reactions.
  • Understanding reaction mechanisms is key to catalyst optimization.

Purpose of the Study:

  • To elucidate the mechanistic pathway of aryldiazonium salt and alkynyl-silane coupling catalyzed by an Au(I) complex.
  • To investigate the role of photophysical processes and electron transfer in the catalytic cycle.
  • To explore strategies for enhancing catalytic efficiency and cost-effectiveness.

Main Methods:

  • Integrated computational strategy combining MS-CASPT2 and DFT.
  • Kinetic analyses of photophysical processes (fluorescence, phosphorescence, ISC, IC).
  • Analysis of electron transfer (ET) and reaction energetics.

Main Results:

  • A four-state photophysical model (S0, S1, T2, T1) was identified.
  • The reaction proceeds via a triplet-state mechanism initiated by single electron transfer (SET).
  • Electron-withdrawing groups on aryldiazonium salts enhance SET efficiency by reducing reorganization energy.

Conclusions:

  • Nonradiative decay is dominant along the reaction coordinate.
  • The SET modulation strategy can be extended to Ag and Cu complexes for efficient and cost-effective C-C coupling.
  • Fundamental structure-reactivity relationships were established for Au-photocatalyzed cross-couplings.